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The name the Belmonts was derived from the fact that two of the four singers lived on Belmont Avenue in the Bronx, and the other two lived near Belmont Avenue.

After unsuccessful singles on Mohawk Records in 1957 and then on Jubilee Records ("The Chosen Few" Dion & the Timberlanes not the Belmonts), Dion was paired with The Belmonts. The group signed with Laurie Records in early 1958. The breakthrough came when their very first Laurie release, "I Wonder Why", reached No. 22 on the Billboard Top 100charts, and they appeared for the first time on the nationally televised American Bandstand show, hosted by Dick Clark. Dion said of the Belmonts, "I'd give 'em sounds. I'd give 'em parts and stuff. That's what 'I Wonder Why' was about. We kind of invented this percussive rhythmic sound. If you listen to that song, everybody was doing something different. It was totally amazing. When I listen to it today, often times I think, 'Man, those kids are talented'."[1] Dion and the Belmonts were the sound of the city. Their roots were doo-wop groups like the Flamingos, the Five Satins, the Dells, acts who developed their sound in urban settings on street corners, mimicking instruments with their voices, even complex jazz arrangements.[2]

They followed the hit with the ballads "No One Knows" (No. 19) and "Don’t Pity Me" (No. 40), which they also performed on Bandstand. This early success brought them their first major tour in late 1958, with the Coasters, Buddy Holly and Bobby Darin, followed by the historic and tragic Winter Dance Party tour featuring Holly, Ritchie Valens and the Big Bopper. On February 2, 1959, after playing the Surf Ballroom, Holly arranged to charter a plane. Dion decided he couldn't afford the $36 cost to fly to the next venue. According to Dion, $36 was the same price his parents paid for monthly rent. He told Holly no. Shortly after midnight, on February 3rd 1959, the plane crashed near Clear Lake, Iowa, with Holly, Valens, The Big Bopper, and the pilot, Roger Peterson, all being killed. Bobby Vee, then an unknown artist, performed in Holly’s place at the very next concert. Later, Jimmy Clanton, Frankie Avalon, and Fabian were hired to finish the tour in place of the three deceased headliners. As of January 11, 2017 with the death of Holly's tour guitarist Tommy Allsup, Dion is the lone surviving member of the original Winter Dance Party lineup (The lone surviving Belmont, Angelo D'Aleo, was not on the tour as he was in the Army at the time).

In March 1959 Dion and the Belmonts’ next single, "A Teenager in Love", broke the Top Ten, reaching No. 5 on the Billboard Hot 100 and No. 28 on the UK Singles Charts. Written by Doc Pomus and Mort Shuman, it's considered one of the greatest songs in Rock and Roll history. It was followed by their first album, "Presenting Dion and the Belmonts". Their biggest hit, "Where or When", was released in November 1959, and reached No. 3 on the Billboard Hot 100 with the group making another national appearance on American Bandstand. The flip side, "That's My Desire", although never charting nationally, is as well known in many areas, especially New York City.

Other singles released for the group that year continued to chart Billboard, but were less successful. In early 1960, Dion checked into a hospital for heroin addiction, a problem he had since his mid-teens. At the height of the group's success his drug dependency worsened. When, "Where or When", peaked, he was in a hospital detoxifying.[3] In addition, there were financial and musical differences between Dion and members of the Belmonts. "They wanted to get into their harmony thing, and I wanted to rock and roll," said Dion. "The label wanted me doing standards. I got bored with it quickly. I said, I can't do this. I gotta play my guitar. So we split up and I did "Runaround Sue", "The Wanderer", and "Ruby Baby".[1] In October 1960, DiMucci decided to quit for a solo career. Now simply known as "Dion", his first major hit, "Lonely Teenager" was backed by a female chorus. He eventually chose to work with The Del-Satins, who backed him (uncredited) on all his early Laurie and Columbia Records hits, which, besides the three aforementioned hits Dion quoted, also included "Donna the Prima Donna" ,"Drip Drop" , "Lovers Who Wander" , and "Little Diane" . Later reissues of these songs would often be erroneously attributed to Dion and the Belmonts. The Belmonts also continued to release records on their own label, Sabina Records, but with less success, although songs like "Such a Long Way", "Tell Me Why", "I Need Someone", "I Confess", and "Come On Little Angel" all got significant radio play in the New York City area.

The group in 1966.

Dion and the Belmonts reunited in late 1966 for the album Together Again on ABC Records. Produced by "DiMont Music", two singles were released from the LP, "My Girl The Month of May" / "Berimbau", and "Movin' Man" / "For Bobbie". Neither charted in the United States, but fared better in England. "My Girl The Month Of May" broke the "Radio London Fab 40" top ten at No. 9 the week of December 25, 1966. One reviewer stated, "some British radio DJ's gave it a lot of airplay at the time." The follow up, "Movin Man", reached No. 17 on the "Radio London" charts on March 26, 1967. "My Girl The Month Of May", was later covered by English artists Alan Bown in 1967, and by The Bunch (featuring Sandy Denny of Fairport Convention) in April 1972. During their brief mid 60's reunion, Dion and the Belmonts appeared on the popular "Clay Cole Show" performing "Berimbau" and "My Girl The Month of May", and occasionally performed at local New York City clubs such as "The Mardi Gras" on Staten Island (April 29, 1967) before disbanding. The original group reunited once again June 2, 1972 for a show at Madison Square Garden, which was recorded and released as a live album for Warner Brothers. A year later, in 1973, DiMucci, Mastrangelo, Milano and D'Aleo performed once more, doing a sold out concert at the Nassau Coliseum on Long Island, New York. No recording of the 1973 reunion was ever released.

In 1968, as a solo performer, Dion recorded "Abraham, Martin and John" written by Dick Holler. It is a tribute to social change icons, Abraham Lincoln, Martin Luther King, Jr., John F. Kennedy and Robert F. Kennedy. It was written as a response to the assassination of King and the younger Kennedy in April and June 1968. When producer Phil Gernhard initially presented the song to DiMucci, the latter didn't care for it. With the persistence of Gernhard, and Dion's wife Susan, he flew to New York that summer. He recorded the song in just one take. Laurie Records released the single in September of that year and it quickly raced up the charts, peaking at number four in December. DiMucci, now a star again, was invited to sing this comeback hit on The Smothers Brothers Comedy Hour, as well as many other top shows.

Including Billboard Hot 100 singles, Dion and the Belmonts charted 856 radio station surveys across the United States during the 1950s and 1960s.[4] In 2000 the group was inducted in the Vocal Group Hall of Fame. Dion (without The Belmonts) was inducted into the Rock and Roll Hall of Fame in 1989.[5]

In 2012, the Rock and Roll Hall of Fame did a mass induction of six deserving pioneering groups that were left out in error when their lead singers were inducted in the Hall of Fame's early years of inductions: the Miracles (Smokey Robinson), the Crickets (Buddy Holly), the Midnighters (Hank Ballard), the Famous Flames (James Brown), the Comets (Bill Haley) and the Blue Caps (Gene Vincent) . Because of the timeline when these groups were successful, it was believed that the Belmonts would be included in this induction, but none was forthcoming. Because of the fact that the Belmonts scored chart hits for an additional three years after Dion left the group, coupled with the fact that the entire group, including Dion, were inducted intact into the Vocal Group Hall of Fame in 2000, 11 years after Dion's solo induction into the Rock Hall, made their omission even more puzzling.[6][7][8] In January 2012, the year of that mass vocal group induction, Fred Milano of the Belmonts died (January 1, 2012). In a Billboard Magazine article, dated January 3, 2012, it was stated: "There was strife between DiMucci and Belmonts members, who were not pleased when DiMucci was inducted into the Rock and Roll Hall of Fame without them in 1989."[9] Carlo Mastrangelo died on April 4, 2016.

Reunion: Live at Madison Square Garden (June 2, 1972) Released in 1973 by Warner Brothers Records

The two Laurie Records LPs are the most collectible, especially the first pressings of "Presenting Dion and the Belmonts", issued as Laurie LLP-1002 (later reissued as LLP-2002). There were also later compilations, some of which included the separate hits of The Belmonts, and some that included the hits of Dion, and Dion and The Belmonts.